Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Veratroyl chloride | HCID 77070 | — |
| Reactant | 5-(chloromethyl)-2-phenyl-1,3-oxazolidine | HCID 270701 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 20489855 | HCID 20489855 | 72.3% |
Reaction Steps
At a temperature of -40° C., a solution of 15.2 g 3,4-dimethoxybenzoyl chloride in 40 ml of chloroform is added dropwise to a solution of 15.0 g of 2-phenyl-5-chloromethyloxazolidine in a mixture of 200 ml of chloroform and 6 ml of pyridine. The mixture is heated to room temperature. After a reaction period of 14 hours, 20 ml of concentrated hydrochloric acid are added, the phases are thoroughly mixed for 10 minutes, and then separated. The separated aqueous phase is diluted with water to twice its volume and is saturated with sodium chloride. Then it is extracted with chloroform. After drying the chloroform extract and evaporating the solvent, 15.0 g of N-(3,4-dimethoxybenzoyl)-3-chloro-1-aminopropan-2-ol is obtained as an oil which can be used in the following reaction without any prior purification. After crystallization from ethanol/toluene, the compound melts at 104°-106° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04177287 |
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| Source dataset | uspto-grants-1979_12 |
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| ORD ID | ord-b064941fb30345fd899bfcbda2f683e0 |
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| Source note | uspto-grants-1979_12 |
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